Wang Jing-Yi, Gao Cong-Hui, Ma Cheng, Wu Xin-Yue, Ni Shao-Fei, Tan Wei, Shi Feng
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, China.
Department of Chemistry, Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province, Shantou University, Shantou, 515063, China.
Angew Chem Int Ed Engl. 2024 Feb 19;63(8):e202316454. doi: 10.1002/anie.202316454. Epub 2024 Jan 15.
In the chemistry community, catalytic asymmetric synthesis of furan-based compounds bearing both axial and central chirality has proven to be a significant but challenging issue owing to the importance and difficulty in constructing such frameworks. In this work, we have realized the first catalytic asymmetric synthesis of five-five-membered furan-based compounds bearing both axial and central chirality via organocatalytic asymmetric (2+4) annulation of achiral furan-indoles with 2,3-indolyldimethanols with uncommon regioselectivity. By this strategy, furan-indole compounds bearing both axial and central chirality were synthesized in high yields with excellent regio-, diastereo-, and enantioselectivities. Moreover, theoretical calculations were conducted to provide an in-depth understanding of the reaction pathway, activation mode, and the origin of the selectivity.
在化学领域，由于构建同时具有轴手性和中心手性的基于呋喃的化合物框架具有重要性和难度，其催化不对称合成已被证明是一个重大但具有挑战性的问题。在这项工作中，我们通过非手性呋喃吲哚与2,3-吲哚二甲醇的有机催化不对称(2+4)环化反应，以不寻常的区域选择性，首次实现了同时具有轴手性和中心手性的五元-五元基于呋喃的化合物的催化不对称合成。通过该策略，以高收率、优异的区域选择性、非对映选择性和对映选择性合成了同时具有轴手性和中心手性的呋喃吲哚化合物。此外，还进行了理论计算，以深入了解反应途径、活化模式和选择性的起源。
